WO2013178668A2 - Solutions tensioactives contenant des n-méthyl-n-oleylglucamines et des n-méthyl-n-c12-c14-acylglucamines - Google Patents

Solutions tensioactives contenant des n-méthyl-n-oleylglucamines et des n-méthyl-n-c12-c14-acylglucamines Download PDF

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Publication number
WO2013178668A2
WO2013178668A2 PCT/EP2013/061044 EP2013061044W WO2013178668A2 WO 2013178668 A2 WO2013178668 A2 WO 2013178668A2 EP 2013061044 W EP2013061044 W EP 2013061044W WO 2013178668 A2 WO2013178668 A2 WO 2013178668A2
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WIPO (PCT)
Prior art keywords
weight
methyl
alkyl
component
acylglucamines
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PCT/EP2013/061044
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German (de)
English (en)
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WO2013178668A3 (fr
Inventor
Peter Klug
Franz-Xaver Scherl
Carina Mildner
Eva-Maria KEITZL
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Clariant International Ltd.
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Filing date
Publication date
Application filed by Clariant International Ltd. filed Critical Clariant International Ltd.
Priority to CN201380028734.4A priority Critical patent/CN104540550A/zh
Priority to US14/401,796 priority patent/US9504636B2/en
Priority to EP13726187.1A priority patent/EP2866895B1/fr
Priority to BR112014029754A priority patent/BR112014029754B1/pt
Priority to JP2015514479A priority patent/JP6525870B2/ja
Priority to ES13726187.1T priority patent/ES2604840T3/es
Publication of WO2013178668A2 publication Critical patent/WO2013178668A2/fr
Publication of WO2013178668A3 publication Critical patent/WO2013178668A3/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/596—Mixtures of surface active compounds

Definitions

  • the invention relates to surfactant solutions containing N-methyl-N-oleylglucamine and N-methyl-N-Ci 2 -Ci 4 -acylglucamine and cosmetic compositions containing these N-methyl-N-acylglucamine.
  • WO 95/17880 discloses a hair shampoo composition containing alkyl glycol ether sulfates and alkyl sulfates and polyhydroxyalkyl fatty acid amides.
  • alkyl glycol ether sulfate u.a. Lauryltriethylene glycol ether sulfate, as the alkyl sulfate is used i.a. Called lauryl sulfate.
  • R 1 is preferably C 1 -C 4 -alkyl, in particular methyl
  • R 2 is preferably straight-chain CyCig-alkyl or alkenyl, in particular straight-chain C 1 -C 6 -alkyl or -alkenyl
  • Z is in particular 1-deoxyglucityl, 2 Deoxyfructityl, 1-Deoxymaltityl, 1-Deoxylactityl, 1-Deoxygalactityl, 1-Deoxymannityl or 1-Deoxymaltotriothityl.
  • the examples disclose hair shampoo compositions containing ammonium lauryl sulfate, ammonium lauryl triethylene glycol sulfate and lauryl N-methylglucamide.
  • WO 95/19415 discloses mixtures of a) N-acyl-N-methylglucamines having a Cs-Cio acyl radical and b) N-acyl-N-methylglucamines having a Ci 2 -Ci 8 acyl radical, in particular a Ci 2 -Ci 4 acyl.
  • Components a) and b) in the mixtures are in the ratio a) to b) of 80:20 to 20:80, in particular in the ratio of 25:75 to 40:60 contain.
  • the surfactant mixtures should have improved surface-active properties and may contain other anionic, nonionic, cationic and amphoteric surfactants. The use is disclosed in hair shampoos, hair lotions and bubble baths.
  • Glucamines are solids with melting points of about 85 ° C (Ci 2 -C 4 acylglucamine containing 10 wt .-% propylene glycol) and about 85 ° C (Ci 6 -C 8 acylglucamine containing 20 wt .-% propylene glycol) , The corresponding pure substances even have significantly higher melting points.
  • C 2 -C 4 acylglucamines when diluted with water, generally form poorly water-soluble gels. Thus, the dilution of these N-acyl-N-methylglucamine in water leads down to 2 wt .-% solutions to form a gel phase, which greatly complicates the handling of these surfactants.
  • N-methyl-N-acylglucamines have the formula (I),
  • R is an alkyl or mono- or polyunsaturated alkenyl radical.
  • the object of the invention is to provide concentrated surfactant solutions containing acylglucamines which do not cause gelation when diluted with water.
  • the surfactant solutions of the invention generally have a melting point of ⁇ 40 ° C and are therefore pumpable in the warmed state and easy to handle on an industrial scale.
  • the N-methyl-N-acylglucamine contained in the surfactant solutions according to the invention contain 5 to 20 wt .-% of N-methyl-N-acylglucamine containing an oleyl group.
  • the proportion of N-methyl-N-acylglucaminen containing an oleyl group at 6 to 18 wt .-%, particularly preferably 7 to 15 wt .-%, based on the amount of all N-methyl-N-acylglucamine ,
  • N-methyl-N-acylglucamine contain from 50 to 95 wt .-% N-methyl-N-acylglucamine containing a Ci 2 -Ci4-acyl group. These are derived from lauric and myristic acid. Preferably, this proportion is 60 to 90 wt .-%, particularly preferably 70 to 85 wt .-%, based on the amount of all N-methyl-N-acylglucamine.
  • N-methyl-N-acylglucamine contained in the surfactant solutions according to the invention contain from 0 to 30% by weight of further N-methyl-N-acylglucamines derived from short-chain and / or long-chain fatty acids, in particular those which are C 1 -C 4 acyl, Ce acyl, C 8 acyl, Cio acyl, Cie acyl, cis acyl (except oleyl) and / or C 2 o acyl included.
  • This proportion is preferably 5 to 25 wt .-%, particularly preferably 7 to 20 wt .-%, based on the amount of all N-methyl-N-acylglucamine.
  • the N-methyl-N-acylglucamine can, as described in EP 0 550 637 Bl, be prepared by reacting the corresponding fatty acid esters or fatty acid ester mixtures with N-methylglucamine in the presence of a solvent having hydroxyl groups or alkoxy groups.
  • Suitable solvents are, for example, C 1 -C 4 -monoalcohols, ethylene glycol, 1,2-propylene glycol, glycerol and alkoxylated alcohols. Preference is given to 1,2-propylene glycol.
  • N-methylglucamine can, as also in EP 0 550 637 AI, can be obtained by reductive amination of glucose with methylamine.
  • Suitable fatty acid esters which are reacted with the N-methylglucamines to form N-methyl-N-acylglucamines are generally the methyl esters which are obtained by transesterification from natural fats and oils, for example the triglycerides.
  • Suitable raw materials for the preparation of fatty acid methyl esters are, for example, coconut oil or palm oil.
  • the surfactant solutions of the invention may contain as component (b) one or more alcohols.
  • Suitable alcohols are water-miscible monoalcohols or diols. Preferred are ethanol, 1, 2-propylene glycol, glycerol, 1, 3-propylene glycol and isopropanol.
  • the surfactant solutions have no monoalcohol. But you can contain diols such as 1, 2-propylene glycol.
  • additives may be contained in the surfactant solutions according to the invention: preservatives, complexing agents and neutralizing agents and buffers such. Citric acid or citric acid salts.
  • the surfactant solution according to the invention contains
  • the invention also provides the use of the surfactant solutions for the preparation of cosmetic compositions.
  • the preparation of the cosmetic compositions comprises the step of diluting the surfactant solutions with water.
  • the surfactant solutions according to the invention are diluted with water in a ratio of 1: 1 to 1:50, preferably 1: 2 to 1:10.
  • the surfactant solutions are diluted to such an extent that the final concentration of N-methyl-N-acylglucamine is in the range from 1 to 10% by weight, preferably in the range from 2 to 5% by weight.
  • the invention also relates to concentrated compositions containing
  • component (A) the sum of components (a1), (a2) and (a3) being 100% by weight, as component (A),
  • compositions contain:
  • the other surfactants (B) may be nonionic surfactants, anionic surfactants, cationic surfactants and betaine surfactants.
  • Suitable anionic surfactants are (C 10 -C 22) -alkyl and alkylene carboxylates, alkyl ether carboxylates, fatty alcohol sulfates, fatty alcohol ether sulfates, alkylamide sulfates and sulfonates, fatty acid alkylamide polyglycol ether sulfates, alkanesulfonates and hydroxyalkanesulfonates, olefin sulfonates, acyl esters of isethionates, alpha-sulfofatty acid esters, alkylbenzenesulfonates, alkylphenol glycol ether sulfonates, Sulfosuccinates, sulfosuccinic monoesters and diesters, fatty alcohol phosphates, fatty
  • compositions contain one or more anionic surfactants from the group of alkyl sulfates and alkyl ether sulfates.
  • alkyl sulfates are the Cs-C2o alkyl sulfates, in particular the linear C8-C20 alkyl sulfates in the form of their sodium, potassium or ammonium salts.
  • alkyl sulfates are lauryl sulfate, coconut alkyl sulfate and tallow alkyl sulfate. Particularly preferred is lauryl sulfate.
  • Preferred alkyl ether sulfates are the C 8 -C 20 -alkyl ether sulfates, with particular preference being given to the linear C 8 -C 20 -alkyl ether sulfates, in particular the alkyl glycol ether sulfates derived from the ethoxylated fatty alcohols, in the form of their sodium, potassium or ammonium salts.
  • alkyl ether sulfates are lauryl ether sulfate, coconut alkyl ether sulfate and tallow alkyl ether sulfate.
  • glycol ether sulfates are lauryl triethylene glycol ether sulfate, coconut alkyl triethylene glycol ether sulfate and tallow alkyl hexa ethylene glycol ether sulfate. Particular preference is given to lauryl glycol ether sulfate, for example lauryl triethylene glycol ether sulfate.
  • Betaine surfactants contain in the same molecule a cationic group, in particular an ammonium group, and an anionic group, which may be a carboxylate group, sulfate group or sulfonate group.
  • Suitable betaines are alkylbetaines such as cocoobetaine or fatty acid alkylamidopropylbetaines, for example cocoacylamidopropylpropylenedimethylbetaine, C 12 -C 18 -dimethylaminohexanoates or cio-cis-acylamidopropane-dimethylbetaines.
  • the compositions comprise one or more amidopropylbetaines of the general formula (I)
  • R a is a linear or branched saturated C 7 -c2i alkyl group or a linear or branched mono- or polyunsaturated C 7 -C 2 is i-alkenyl group.
  • compositions contain one or more betaines of the formula (II)
  • compositions contain one or more sulfobetaines of the formula (III)
  • R c is a linear or branched saturated C 8 -C 22 alkyl group or a linear or branched mono- or polyunsaturated C 8 -C 22 alkenyl group.
  • compositions contain one or more betaine surfactants selected from the group of compounds consisting of the amidopropylbetaines of the formula (I), the betaines of the formula (II) and the sulphobetaines of the formula (III).
  • the compositions contain one or more betaine surfactants selected from the amidopropylbetaines of the formula (I).
  • compositions contain one or more betaine surfactants selected from the betaines of the formula (II).
  • compositions contain one or more betaine surfactants selected from the sulfobetaines of the formula (III).
  • the radical R a in the one or more amidopropyl betaines of the formula (I) is a linear or branched saturated Cy-Cn-alkyl group.
  • the linear and branched saturated alkyl groups R a are preferred.
  • amidopropylbetaines of the formula (I) are particularly preferably cocamidopropylbetaines.
  • the radical R b in the one or more betaines of the formula (II) is a linear or branched saturated Cs-Cis-alkyl group and particularly preferably a linear or branched saturated C 12-C 18 -alkyl group.
  • the linear saturated alkyl groups R b are preferred.
  • the radical R c in the one or more sulfobetaines of the formula (III) is a linear or branched saturated Cs-Cis-alkyl group and particularly preferably a linear or branched saturated C 12-C 18 -alkyl group.
  • the linear saturated alkyl groups R c are preferred.
  • aqueous surfactant solutions particularly preferably contain amidopropylbetaines of the formula (I) and / or alkylbetaines of the formula (II).
  • the compositions contain a betaine surfactant in addition to the anionic surfactant.
  • the compositions contain the alkyl sulfates and / or alkyl ether sulfates and betaine surfactants described above.
  • Suitable cationic surfactants are substituted or unsubstituted straight-chain or branched quaternary ammonium salts of the type R 1 N (CH 3 ) 3 X, R 1 R 2 N (CH 3 ) 2 X, R 1 R 2 R 3 N (CH 3 ) X or R ! R 2 R 3 R 4 NX.
  • the radicals R 1, R 2, R 3 and R 4 may preferably independently unsubstituted alkyl having a chain length of between 8 and 24 carbon atoms, in particular between 10 and 18 carbon atoms, hydroxyalkyl of 1 to 4 carbon atoms, phenyl, C 2 to Cis alkenyl, C 7 to C 24 aralkyl, (C 2 H 4 O) x H wherein x is from 1 to 3, one or more ester group-containing alkyl groups or cyclic quaternary ammonium salts.
  • X is a suitable anion.
  • (C 8 -C 22 ) -alkyltrimethylammonium chloride or bromide particularly preferably cetyltrimethylammonium chloride or bromide, di (C 8 -C 22 ) -alkyldimethylammonium chloride or bromide, (C 8 -C 22 ) -alkyldimethylbenzylammonium chloride or bromide, (C 8 -C 22 ) -alkyl-dimethylhydroxyethyl-ammonium chloride, -phosphate, -sulfate, -lactate, more preferably distearyldimethyl-ammonium chloride, di (C 8 -C 22 ) -alkylamidopropyltrimethylammonium chloride and -methosulfate.
  • Suitable nonionic surfactants are, for example, the following compounds:
  • Polyethylene, polypropylene and polybutylene oxide condensates of alkylphenols.
  • These compounds include the condensation products of alkylphenols having a C 6 to C 2 o alkyl group, which may be either linear or branched, with alkene oxides.
  • These surfactants are as alkylphenol alkoxylates, eg
  • the alkyl or alkenyl chain of the aliphatic alcohols may be linear or branched, primary or secondary, and generally contains from 8 to 22
  • Carbon atoms Particularly preferred are the condensation products of Cio to C 2 o alcohols with 2 to 18 moles of ethylene oxide per mole of alcohol.
  • the alcohol ethoxylates may have a narrow (“narrow range ethoxylates") or a broad homolog distribution of the ethylene oxide (“Broad Range Ethoxylates"). Examples of commercially available nonionic surfactants of this
  • Type are Tergitol ® 15-S-9 (the condensation product of a linear secondary Cn-Cis alcohol with 9 moles ethylene oxide), Tergitol ® 24-L-NMW (Condensation product of a linear primary C12-C14 alcohol with 6 moles of ethylene oxide with a narrow molecular weight distribution).
  • This product class also includes the Genapol ® brands from Clariant. Condensation products of ethylene oxide having a hydrophobic base formed by condensation of propylene oxide with propylene glycol. The hydrophobic part of these compounds preferably has a molecular weight between 1500 and 1800. The addition of ethylene oxide to this hydrophobic part leads to an improvement in water solubility.
  • the product is liquid up to a polyoxyethylene content of about 50% of the total weight of the product
  • Condensation product which corresponds to a condensation with up to about 40 moles of ethylene oxide.
  • Commercially available examples of this product class are the Pluronic ® brands from BASF and the Genapol ® PF brands from Clariant.
  • Propylene oxide and ethylenediamine The hydrophobic moiety of these compounds consists of the reaction product of ethylenediamine with excess propylene oxide and generally has a molecular weight of 2500 to 3000. Ethylene oxide is added to this hydrophobic unit to a content of 40 to 80 wt .-% polyoxyethylene and a molecular weight of 5000 to 11000.
  • Commercially available examples of this class of compounds are the Tetronic ® brands of BASF and Genapol ® PN brands of Clariant.
  • nonionic surfactants are alkyl and Alkenyloligoglycoside and Fettchurepolyglykolester or Fettammpolyglykolester having in each case 8 to 20, preferably 12 to 18 carbon atoms in the fatty alkyl, Alkyloligoglycoside, Alkenyloligoglycoside and fatty acid N-alkylglucamine.
  • the surfactant solutions of the invention may contain as component (C) one or more alcohols derived from the surfactant solution according to the invention.
  • Suitable alcohols are the abovementioned water-miscible alcohols.
  • the compositions do not contain monoalcohols.
  • Auxiliaries and additives (E) are, for example, preservatives, fragrances, dyes and restreasers.
  • Suitable preservatives are the preservatives listed in the appended appendix to the European Cosmetics Act, for example phenoxyethanol, benzyl alcohol, parabens, benzoic acid and sorbic acid; for example, 1,3-bis (hydroxymethyl) -5,5-dimethylimidazolidine-2,4-dibutyl is particularly suitable. dione (Nipaguard DMDMH ®).
  • the amount of preservatives in the compositions according to the invention is generally from 0 to 2% by weight, based on the total weight of the finished compositions.
  • compositions according to the invention are in the form of concentrates for the preparation of products for hair and skin cleansing, such as hair shampoos, shower baths, hand soaps and facial cleansers.
  • hair shampoos such as hair shampoos, shower baths, hand soaps and facial cleansers.
  • shower baths such as hand soaps and facial cleansers.
  • facial cleansers such as hair shampoos, shower baths, hand soaps and facial cleansers.
  • N-acyl-N-methylglucamine described below were prepared according to EP 0 550 637 from the corresponding fatty acid methyl esters or triglycerides and N-methylglucamine in the presence of 1,2-propylene glycol as a solvent and as a solid consisting of active substance and 1,2-propylene glycol obtained (all data in% by weight).
  • compositions of Examples 1 to 4 according to the invention are not only easy to handle, but also easily dilutable in water without gelling.

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  • Life Sciences & Earth Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
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  • Dermatology (AREA)
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Abstract

L'invention concerne une solution tensioactive contenant : (a) 28 à 65 % en poids d'un mélange de (a1) 5 à 20 % en poids de N-méthyl-N-oleylglucamine, (a2) 50 à 93 % en poids de N-méthyl-N-C12-C14-acylglucamines, (a3) 0 à 30 % en poids d'autres N-méthyl-N-acylglucamines, la somme des constituants (a1), (a2) et (a3) étant égale à 100 % en poids, (b) 0 à 20 % en poids d'au moins un alcool, (c) 20 à 72 % en poids d'eau, (d) 0 à 5 % en poids d'additifs, la somme des constituants (a), (b), (c) et (d) étant égale à 100 % en poids.
PCT/EP2013/061044 2012-05-30 2013-05-29 Solutions tensioactives contenant des n-méthyl-n-oleylglucamines et des n-méthyl-n-c12-c14-acylglucamines WO2013178668A2 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
CN201380028734.4A CN104540550A (zh) 2012-05-30 2013-05-29 包含n-甲基-n-油烯基葡糖胺和n-甲基-n-c12-c14-酰基葡糖胺的表面活性剂溶液
US14/401,796 US9504636B2 (en) 2012-05-30 2013-05-29 Surfactant solutions containing N-methyl-N-oleylglucamines and N-methyl-N-C12-C14-acylglucamines
EP13726187.1A EP2866895B1 (fr) 2012-05-30 2013-05-29 Solutions tensioactives contenant des n-méthyl-n-oleylglucamines et des n-méthyl-n-c12-c14-acylglucamines
BR112014029754A BR112014029754B1 (pt) 2012-05-30 2013-05-29 soluções de tensoativos que contêm n-metil-noleilglucaminas e n-metil-n-c12-c14 acilglucaminas e seu uso, processo para produzir composições cosméticas e composição
JP2015514479A JP6525870B2 (ja) 2012-05-30 2013-05-29 Ｎ−メチル−ｎ−オレイルグルカミン及びｎ−メチル−ｎ−ｃ１２〜ｃ１４−アシルグルカミンを含む界面活性剤溶液
ES13726187.1T ES2604840T3 (es) 2012-05-30 2013-05-29 Soluciones tensioactivas que contienen N-metil-N-oleil-glucaminas y N-metil-N-(acil de C12-C14)-glucaminas

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102012010701 2012-05-30
DE102012010701.3 2012-05-30

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WO2013178668A2 true WO2013178668A2 (fr) 2013-12-05
WO2013178668A3 WO2013178668A3 (fr) 2014-06-26

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PCT/EP2013/061044 WO2013178668A2 (fr) 2012-05-30 2013-05-29 Solutions tensioactives contenant des n-méthyl-n-oleylglucamines et des n-méthyl-n-c12-c14-acylglucamines

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US (1) US9504636B2 (fr)
EP (1) EP2866895B1 (fr)
JP (1) JP6525870B2 (fr)
CN (1) CN104540550A (fr)
BR (1) BR112014029754B1 (fr)
ES (1) ES2604840T3 (fr)
WO (1) WO2013178668A2 (fr)

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WO2014206555A2 (fr) * 2013-06-28 2014-12-31 Clariant International Ltd Utilisation dans des shampooings de n-alkyl-n-acylglucamines spéciales pour la revitalisation capillaire
WO2014206554A3 (fr) * 2013-06-28 2015-02-19 Clariant International Ltd Utilisation de n-methyl-n-acylglucamines spéciales dans des produits de nettoyage cutané et des détergents pour vaisselle à la main
WO2016062619A1 (fr) * 2014-10-23 2016-04-28 Clariant International Ltd Utilisation de n-alkyl-n-acylglucamines spéciales pour protéger la couleur dans des shampooings
US20160272666A1 (en) * 2013-11-20 2016-09-22 Clariant International Ltd. Partially Crystalline Glucamide Compositions And Method For Preparing Same
EP3181668A1 (fr) 2016-12-02 2017-06-21 Clariant International Ltd Composition comprenant des mélanges de glucamides, procédé pour leur préparation et leur utilisation
EP3241887A1 (fr) * 2016-08-01 2017-11-08 Clariant International Ltd Composition comprenant un éthoxylate d'alcool et de glucamide
EP3670495A1 (fr) 2018-12-21 2020-06-24 Clariant International Ltd Tensioactifs à base de glucamide
US10772324B2 (en) 2012-11-03 2020-09-15 Clariant International Ltd. Aqueous adjuvant-compositions
US10813862B2 (en) 2012-05-30 2020-10-27 Clariant International Ltd. Use of N-methyl-N-acylglucamines as solubilizers
US10864275B2 (en) 2012-05-30 2020-12-15 Clariant International Ltd. N-methyl-N-acylglucamine-containing composition
US10920080B2 (en) 2015-10-09 2021-02-16 Clariant International Ltd. N-Alkyl glucamine-based universal pigment dispersions
US10961484B2 (en) 2015-10-09 2021-03-30 Clariant International Ltd. Compositions comprising sugar amine and fatty acid
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US11220603B2 (en) 2016-05-09 2022-01-11 Clariant International Ltd. Stabilizers for silicate paints
US11306170B2 (en) 2016-12-15 2022-04-19 Clariant International Ltd. Water-soluble and/or water-swellable hybrid polymer
US11311473B2 (en) 2016-12-12 2022-04-26 Clariant International Ltd Use of a bio-based polymer in a cosmetic, dermatological or pharmaceutical composition
US11339241B2 (en) 2016-12-15 2022-05-24 Clariant International Ltd. Water-soluble and/or water-swellable hybrid polymer
US11384186B2 (en) 2016-12-12 2022-07-12 Clariant International Ltd Polymer comprising certain level of bio-based carbon
US11401362B2 (en) 2016-12-15 2022-08-02 Clariant International Ltd Water-soluble and/or water-swellable hybrid polymer
US11425904B2 (en) 2014-04-23 2022-08-30 Clariant International Ltd. Use of aqueous drift-reducing compositions
US11447682B2 (en) 2015-06-17 2022-09-20 Clariant International Ltd Water-soluble or water-swellable polymers as water loss reducers in cement slurries
US11542343B2 (en) 2016-12-15 2023-01-03 Clariant International Ltd Water-soluble and/or water-swellable hybrid polymer

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EP2866895A2 (fr) 2015-05-06
WO2013178668A3 (fr) 2014-06-26
CN104540550A (zh) 2015-04-22
EP2866895B1 (fr) 2016-08-31
JP2015523972A (ja) 2015-08-20
US9504636B2 (en) 2016-11-29
BR112014029754A2 (pt) 2017-06-27
BR112014029754B1 (pt) 2020-04-28

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